HIGH FIDELITY inspires our own desert island, all-time, top 5 cinematic sad sacks

The lovable losers in Stephen Frears’ HIGH FIDELITY waste their days sitting around the Chicago record store Championship Vinyl compiling Top 5 lists. Records to play on a Monday morning? Dream jobs? Songs about death? These elitist “experts” have got you covered. These guys have perfected the art of pining after the prettiest girls. In the best-case scenarios, they even win that girl’s heart.

And yes, we double-dipped on Cusack, because few in Hollywood are quite as masterful at the hangdog look of the broken-hearted, unfulfilled Romeo. It’s his calling card … as HIGH FIDELITY confirms.

1. Woody Allen, ANNIE HALL
Probably the unofficial Godfather of awkward, sad-sack leading men, Allen built an entire career out of writing and directing uncomfortable romances around himself and others playing nebbish men dreaming about being with the perfect woman. Though you could single out virtually any movie on Allen’s stout resume, I’m opting for ANNIE HALL, the Oscar winner that established the director’s formidable formula.

2. Paul Giamatti, SIDEWAYS
Giamatti is brilliant character actor who has successfully perfected, on multiple occasions, the rhythms and cadences of the defeated romantic. Miles, the wine-chugging loner at the heart of Alexander Payne’s empathetic drama, might be his most well-rounded creation, pairing the unusually sensitive actor with an ideal counterpart in Thomas Haden Church’s Jack, a horndog driven only by his need to bed the closest hottie. We happily cheer on his attempts to connect with the free-spirited Maya (Virginia Madsen). Just don’t serve him any Merlot!

3. Ernest Borgnine, MARTY
An early example of the Hollywood schlub, Ernest Borgnine’s Marty Piletti is a quiet, unassuming butcher who actually gets the girl (Betsy Blair, in this instance), but almost lets her walk away thanks to misguided criticisms from his lonely control freak of a mother (Esther Minciotti). Paddy Chayefsky’s storybook for MARTY brought tears to the eyes of every Average Joe who saw themselves in Borgnine’s lovable loser. Try not to cheer when he picks up a phone and, in one of the film industry’s most memorable closing scenes, asks, “Hello, Clara?”

4. John C. Reilly, CHICAGO
I almost went with William H. Macy’s character from BOOGIE NIGHTS, who has to watch his wife in an uncompromising position on the family’s driveway. But I was reminded of Macy’s NIGHTS co-star, John C. Reilly, and his heartbreakingly invisible performance as Amos Hart in Rob Marshall’s CHICAGO, and I had to add him to the list. Hart is a stepping-stone for his fame-seeking spouse, Roxy (Renee Zellweger). And he knows it, which is twice as devastating for the audience. You can look right through him, walk right by him, but it’s impossible not to know a performer of Reilly’s talents is there.

5. John Cusack, SAY ANYTHING …
Cusack’s HIGH FIDELITY character, Rob Gordon, feels like Lloyd Dobler all grown up. Well, not grown up. Just older. Still reflective. Obsessed with the opposite sex. And sad. Deep down, just really, really sad. I’m confident this is one of the reasons why audiences took to HIGH FIDELITY the way that they did back in 2000. It was an excuse to spend more time with Cusack’s adorably misguided Dobler character — just in a different form. The actor doesn’t wear this uncomfortable emotional suit that often, but when he does, it fits him like a glove.